ammonia in tetrahydrofuran T=-78 - 25°C; 48 h;

1.1: 100 percent / Et3N / CH2Cl2 / 1 h / 20 °C 2.1: POCl3 / 1 h / 0 °C 2.2: 99 percent / 3 h / 25 °C 3.1: 100 percent / pyridine / 12 h / 25 °C 4.1: 12.8 mg / MnO2; pyridine / benzene / 2 h / 65 °C 5.1: 67 percent / Dess-Martin periodinane; H2O / CH2Cl2 / 12 h / 25 °C 6.1: 95 percent / NH3 / tetrahydrofuran / 48 h / -78 - 25 °C View Scheme

1: 1.) potassium hydride / 1) DMF, room temperature, 45 min; 2) 0 deg C --> room temperature, 1 h 2: 97 percent / diethyl ether / 0.33 h / Ambient temperature 3: 88 percent / Bu3SnH, AIBN / benzene / 0.75 h / Heating 4: 94 percent / Lawesson's reagent / benzene / 1 h / Heating 5: ethanol / 0.25 h / Heating 6: potassium nitrosodisulfate, sodium dihydrogen phosphate / acetone; H2O 7: 72 percent / NH3 / CH2Cl2 / 96 h / Ambient temperature View Scheme

1: 97 percent / diethyl ether / 0.33 h / Ambient temperature 2: 88 percent / Bu3SnH, AIBN / benzene / 0.75 h / Heating 3: 94 percent / Lawesson's reagent / benzene / 1 h / Heating 4: ethanol / 0.25 h / Heating 5: potassium nitrosodisulfate, sodium dihydrogen phosphate / acetone; H2O 6: 72 percent / NH3 / CH2Cl2 / 96 h / Ambient temperature View Scheme

1: 94 percent / Lawesson's reagent / benzene / 1 h / Heating 2: ethanol / 0.25 h / Heating 3: potassium nitrosodisulfate, sodium dihydrogen phosphate / acetone; H2O 4: 72 percent / NH3 / CH2Cl2 / 96 h / Ambient temperature View Scheme

1: ethanol / 0.25 h / Heating 2: potassium nitrosodisulfate, sodium dihydrogen phosphate / acetone; H2O 3: 72 percent / NH3 / CH2Cl2 / 96 h / Ambient temperature View Scheme

1: potassium nitrosodisulfate, sodium dihydrogen phosphate / acetone; H2O 2: 72 percent / NH3 / CH2Cl2 / 96 h / Ambient temperature View Scheme

1: 88 percent / Bu3SnH, AIBN / benzene / 0.75 h / Heating 2: 94 percent / Lawesson's reagent / benzene / 1 h / Heating 3: ethanol / 0.25 h / Heating 4: potassium nitrosodisulfate, sodium dihydrogen phosphate / acetone; H2O 5: 72 percent / NH3 / CH2Cl2 / 96 h / Ambient temperature View Scheme

1: 72 percent / NaOMe, NaBH4 / methanol; tetrahydrofuran 2: 26 percent / K2CO3 / 2-methoxy-ethanol 3: 42 percent / ZnCl2 / dimethylformamide 4: 54 percent / toluene 5: 71 percent / KOH / ethanol 6: 82 percent 7: 78 percent / CAN / methanol 8: 96 percent / NH4OH / methanol View Scheme

1: 26 percent / K2CO3 / 2-methoxy-ethanol 2: 42 percent / ZnCl2 / dimethylformamide 3: 54 percent / toluene 4: 71 percent / KOH / ethanol 5: 82 percent 6: 78 percent / CAN / methanol 7: 96 percent / NH4OH / methanol View Scheme